3-Methoxyazetidine hydrochloride → 4-(3-methoxy-azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide

HRID 1802285Notes

Reaction equation

HRID 1802285 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:28]=[C:11]3[CH:12]=[C:13]([NH:16][C:17]([C:19]4[N:23]([CH3:24])[N:22]=[CH:21][C:20]=4[C:25]([OH:27])=O)=[O:18])[CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH3:30][O:31][CH:32]1[CH2:35][NH:34][CH2:33]1>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:28]=[C:11]3[CH:12]=[C:13]([NH:16][C:17]([C:19]4[N:23]([CH3:24])[N:22]=[CH:21][C:20]=4[C:25]([N:34]4[CH2:35][CH:32]([O:31][CH3:30])[CH2:33]4)=[O:27])=[O:18])[CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 222428583-Methoxyazetidine hydrochlorideHCID 677752295-(2-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 677754704-(3-methoxy-azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amideYield 14.1%

Procedure

The product was prepared in the same manner as described in example 3 using 5-(2-(3-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (60 mg, 158 μmol) and 3-methoxyazetidine hydrochloride (58.5 mg, 473 μmol) as starting materials. The reaction affords 4-(3-methoxy-azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (10 mg, 14.1%) as white solid. mp.: 255-257° C., MS: m/z=450.0 (M+H+).

Workup

  1. customThe product was prepared in the same manner

Sources & evidence

ORD record
ord-a67e1bdf1e2c4f5a83874c9a234698cb
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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